Synthetic Route of 13924-94-2,Some common heterocyclic compound, 13924-94-2, name is Methyl 5-aminopyrazine-2-carboxylate, molecular formula is C6H7N3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
a. Methyl 5-((3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yI)amino)pyrazine-2- carboxylate (93). To a solution of 77 (1.1303 g, 4.02 mmol), 92 (0.5969 g, 3.90 mmol), CsCO3 (3.12 g, 9.58 mmol), rac-B1NAP (0.1868 g, 0.30 mmol) in toluene (4.5 mL) in a 100 mL round-bottomed flask was added Pd2(dba)3 (0.1780 g, 0.19 mmol). The solution was sparged with nitrogen for 5 mm., then a reflux condenser was fitted to the flask, the atmosphere was evacuated and back-filled with nitrogen (three times), and the reaction was heated to reflux with stirring in an oil bath (125- 120 C) for 22h. After cooling the reaction to room temperature, excess cesium carbonate and other solid particulates were filtered and washed with ethyl acetate, and the organic filtrate was concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, 20% ethyl acetate:hexanes to 25% ethyl acetate: hexanes) to give 93 (0.8727 g, 63%) as a crystalline solid, m.p. 134.9-137.1 C: ?H NMR (400 MHz, CDC13)6 8.81 (d,J= 1.2, 1H), 8.08 (d,J = 1.6, 1H), 7.32 (s, 1H), 7.20 (s, 1H), 7.03 (br s, 1H), 3.95 (s, 3H), 2.22 (s, 3H), 1.68 (s, 4H), 1.28 (s, 6H), 1.24 (s, 6H); ?3C NMR (100.6 MHz, CDC13) 164.8, 154.3, 145.4, 144.1, 143.6, 132.8, 130.7,129.5, 129.3, 122.2, 52.3, 34.9, 34.8, 34.1, 33.9, 31.8, 31.7, 17.6; IR(neat) 3162, 2961, 1712, 1542, 1306, 1271, 1129 cm1 ES-MS (M+Na)+ calcd for C21H27N3O2Na 376.2001, found 376.2006.
The synthetic route of 13924-94-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY; WAGNER, Carl; MARSHALL, Pamela; JURUTKA, Peter; WO2015/130973; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem